In Sounding Out the City, Michael Bull describes how recorded music made portable by the iPod—and the Walkman before it—allows us to “aestheticize urban space.” David Byrne, famed urban cyclist (and member of the Talking Heads), riffed on Bull’s idea in his book, How Music Works:

We carry our own soundtrack with us wherever we go, and the world around us is overlaid with our music. Our whole life becomes a movie, and we can alter the score for it over and over again: one minute it’s a tragedy and the next it’s an action film. Energetic, dreamy, or ominous and dark: everyone has their own private movie going on in their heads, and no two are the same.

Bull describes using these devices to ignore the noise and people in the city. By contrast, Byrne’s book examines how space shapes sounds and their social context. Headphones place music in a vacuum, but the human urge to make music doesn’t happen in one. Byrne describes how people used drums to communicate across open fields or how church halls resonate or how CBGBs squeezed punk music to its rawest form. Place matters because it shapes how we play.

Byrne also describes how hip hop was written to be heard in cars with booming sound systems. “Massive volume seems to be more about sharing your music with everyone, gratis!” he writes. Exactly.

The joy of portability

My particular favorite sound cannon has to be the discontinued iHome iH85 Bike-to-Beach Speaker system. I bought one in 2010 when I was going to school in Philadelphia. Long before Bluetooth speakers were ubiquitous, here was a speaker designed perfectly for a bicycle: a five-button, handle-bar mounted remote for play/pause, volume, and track skipping, and a speaker mounted on a water bottle cage.

It was simple and ahead of its time—before Bluetooth speakers became ubiquitous. My first one cost me $25. The fatal flaw was that the gadget couldn’t survive the oodles of potholes, curbs, and cobblestones I put it through. The second was $80 on eBay after it had been discontinued.

I’ve since retired my Bike-to-Beach for a more janky set up—a Bose SoundLinkthat I use with my iPhone (at my distracted peril) or with a cable from my iPod Classic (at its expensive peril). Regardless, an onslaught of both generally portable and bicycle-specific music speakers confirms what I knew as scrappy college sophomore: biking with beats is fun.

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Fear no danger (but don’t be an idiot)

Henry David Thoreau once said, “When I hear music, I fear no danger. I am invulnerable. I see no foe. I am related to the earliest times, and to the latest.” I can’t describe this feeling better except by example.

I remember blasting the Wu-Tang Clan at midnight as I zipped home along a side street, and the transcendent lift that “A Change Is Gonna Come” gave a group bike ride as Sam Cooke beckoned across the Potomac. It’s the joy of watching heads turn as Led Zeppelin blares from the top of the hill you’re about to dive-bomb down, or the thrill of blasting past strangers who start to dance to some James Brown.

Sometimes it’s corny. Like the playlist I made for my city’s annual naked bike ride, pairing Queen’s “Bicycle Race” with The Beatles’ “Why Don’t We Do It In The Road?” and the Jungle Book’s “Bare Necessities.” Other times, music can be a form of dissent—owing much to the Supreme Court’s description of the sound truck as “the poor man’s printing press”—letting some Public Enemy or Rage Against The Machine or the more mild-mannered ‘60s protest anthems play out on the National Mall. I’ll spare you my bucket list of city-specific song playlists.

Now, a few bits of practical advice:

Beware of soft or quiet songs—drums and electric instruments are key for going up against bustling street sounds. (The Black Keys are kind of perfect for this). Just remember, you don’t have a parental advisory sticker on your bike. Keep Eminem off around the kids.

Extra batteries are nice to have.

Make a playlist. Especially in traffic, you do not want to be fiddling around with a phone every time the wrong song pops up on shuffle. The unpredictable can be embarrassing (“Why is ‘Mambo #5’ playing right now?”), and a song with sound effects like sirens or guns can cause panic, like yelling “fire” in a crowded theater.

Make a plan of where you’re going, especially if you’re rocking and rolling with friends. I almost lost CityLab’s George Joseph at the Jefferson Memorial because I was jamming too hard to Hall and Oates.

When in doubt about a song, pick Aretha Franklin. Anyone who doesn’t like her can get out of town.